Jake Dal Porto: There isn’t a single general manager is baseball that enjoys negotiating with Scott Boras, the man behind many of baseball’s top players. He usually gets his way when the final dominos fall, but he isn’t perfect. Edwin Jackson and Ryan Madson are two examples of Boras’s flawed work of late.

Here’s how they have and will be affected in free agency:

How Edwin Jackson Will Be Affected

Jackson seems to be the MLB’s definition of a journeyman. With ten years under his belt, he has pitched on seven teams, and not once has he signed a contract worth longer than three years. Jackson had an opportunity to erase that trend last off-season with several long-term deals at his disposal. However, Fox Sport’s Ken Rosenthal noted last winter that instead of taking the safe route, he could roll the dice and shoot for a larger contract next winter, which is now this winter. Jackson followed Rosenthal’s blueprint, signing a one-year deal with the Nationals worth $11 million.

Now the question is, will Jackson still have multiple long-term deals thrown his way this off-season, or will his mediocre 2012 campaign force him to stick to the short-term contracts that he fed off of for his entire career?

Jackson is a very peculiar asset in that he can replicate an ace when he’s clicking. He boasts an electric fastball which is backed by a slider that opposing hitters hit just .199 off of this past season. When he’s not clicking, though, he appears as nothing but a thrower and unravels rather quickly. I’d say that is peculiar.

Unfortunately for Jackson, the word is out about his inconsistency. It has been out for years now, given that teams are reluctant to dish out long-term contracts for him. And simply put, his inconsistency is a turnoff for organizations preparing long-term offers for him because they don’t know what side of Jackson they would receive. Usually, players, or more specifically pitchers, who are locked up long-term have displayed some signs of consistency over their respective careers. Boras and his client couldn’t utilize that in Jackson’s last round of negotiations last season. While Jackson apparently received multiple year offers last season, he decided to take the Scott Boras gamble with the one-year deal. Did the gamble pay off?

In 2012, Jackson compiled a 4.03 earned run average and a 3.85 FIP (Fielding Independent Percentage). The journeyman posted the fourth highest WAR on the Nationals’ pitching staff (Wins Above Replacement) with a 2.7 mark. Therefore, he was an important piece to the Nationals. His overall numbers, however, are not appealing on the surface.

According to multiple reports, Jackson would like to return to the Nationals if they can agree on a contract that fits both of their respective terms. For Jackson, his terms consist of a multi-year deal. For the Nationals, the terms would probably be a reasonable annual salary if they agreed to give Jackson a multi-year deal. Basically, Jackson is sacrificing a higher annual salary for a long-term deal.

But, it’s safe to say that Boras screwed Jackson a bit. From his perspective, letting Jackson build his market value on a one-year deal seemed like a good bet last winter, but also a risky one. While he didn’t entirely dampen his value, Jackson certainly took a step back from what could have been a massive payday nearly a year ago. Considering that Scott Boras is no longer representing Edwin Jackson, we have a good idea of what the pitcher thought of his former agent’s work. While the Scott Boras holdout methods work for many of his clients, some unfortunately get lost in the shuffle along the way. Edwin Jackson was one of those unfortunate victims. Now he will need to figure out if that “big payday” will come to him this offseason. It really is now or never for Edwin Jackson.

How Will Ryan Madson Be Affected

Coming off of a season where he didn’t pitch due to Tommy John Surgery, Madson and Boras will be hard pressed to find a team willing to offer him a long-term contract given the risk factor.

Madson signed a one-year six million dollar contract with the Reds last winter before being hindered with an arm injury that slashed his season. The Reds did have an option worth $11 million on the closer, but Madson opted out to become a free agent.

So Madson and Boras are set to test the open waters. What might offset selective suitors is the fact that Madson wants to remain the closer’s role. According to Boras, several teams have already expressed interest in him in that role. A potential return to Philadelphia, where Madson converted 32 of 34 saves in 2011, would be put to sleep if the 32 year-old wants to close games, assuming that the Phillies would stick with Jonathan Papelbon. There are also extreme hurt feelings for Madson after he almost was locked up by the Phillies, only to have the team turn to Papelbon in the 11th hour. Scott Boras went on record as being very upset with the Phillies conduct in the negotiations. Very ironic considering the business practices that Boras has employed over the years. For once, Scott Boras got a taste of his own medicine in a contract that went south. The Phillies were very happy with the results they received from Papelbon. Ryan Madson? He never pitched for the Reds this season and was left to pick up the pieces again. Another Scott Boras gamble that went south. While Edwin Jackson has health and durability on his side, Ryan Madson only has recovery and the hope that he will be healthy to start the year. The $44 million that Madson was supposed to receive from the Phillies over 4 years became $11 million and another kick at the can. Things could not have turned out worse for Ryan Madson.

While Madson has recorded a 2.89 ERA over the past five years, he still has a lot to prove. Some pitchers recover from Tommy John Surgery extremely well, some don’t. Most take at least two years to fully recover and return to form. So with that in mind, teams don’t want to fork over a truckload of money before being assured that he is still the effective pitcher he was prior to enduring surgery. He will be lucky to get one year with an option, at $2-3 million plus incentives. A steep drop from the long term that was supposed to be there for Madson last offseason.

Luckily for Madson, the market for closers this offseason is slim. The Yankees will eventually need someone to takeover for Mariano Rivera, so that is a potential fit. The Reds might try to bring back Madson at a lower price tag, given that they want to put Aroldis Chapman in the rotation as soon as 2013. And if the Royals lose Joakim Soria, Madson could check in to see what their plans are. Of course, the AL champs Tigers don’t intend to bring back Jose Valverde. Given the strong relationship Boras has with the Tigers (see Prince Fielder and Magglio Ordonez signings), a trip to Motown is very likely in Ryan Madson’s future.

Scott Boras didn’t necessarily cost Madson as much as he did with Jackson because it was simply a freak injury. Instead, Madson will simply have to prove himself again before getting an appealing deal. The main difference? Scott Boras will at least get to redeem himself with Madson. Edwin Jackson was done gambling and is ready to take the sure contract. Scott Boras may be extremely intelligent and one of the best agents that the game has ever seen. But in the case of Madson and Jackson, it is clear that the man can make some big blunders as well.

(*The views and opinions expressed in this report are those of the author and do not necessarily reflect the views of mlbreports.com*)

Jake Dal Porto is a Baseball Writer with MLB reports and a student from the Bay Area. Jake’s favorite sports moment was when the Giants won the World Series back in 2010. He loves to use sabermetrics in his work. He thinks they are the best way to show a player’s real success compared to the basic stats such as ERA, RBIs, and Wins. Jake also enjoys interacting and debating with his readers. Follow him on Twitter: Follow @TheJakeMan24

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